Tributylphosphine → HCID 18536026, compound

HRID 412135Notes

Reaction equation

HRID 412135 reaction equation
CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C.C(P(CCCC)CCCC)CCC.[CH2:30]([O:37][C:38]1[CH:39]=[C:40]([C:44]2[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][C:45]=2[NH:51][C:52](=[O:58])[CH2:53][NH:54][CH2:55][CH2:56]O)[CH:41]=[CH:42][CH:43]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1COCC1>[ClH:50].[CH2:30]([O:37][C:38]1[CH:39]=[C:40]([C:44]2[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][C:45]=2[N:51]2[CH2:56][CH2:55][NH:54][CH2:53][C:52]2=[O:58])[CH:41]=[CH:42][CH:43]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 18536097HCID 18536097, compound

Product 1

HCID 18536026HCID 18536026, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of di-tert-butylazodicarboxylate (733 mg, 3.2 mmol) in 5 mL of THF at 0° C. was added tributylphosphine (0.797 mL, 3.2 mmol) dropwise. After 10 minutes, a solution of the product from Step D (895 mg, 2.10 mmol) in 5 mL of THF was added dropwise over 15 minutes, and the reaction was allowed to warm to room temperature. After 16 hours, the solution was concentrated in vacuo. The crude product mixture was purified by silica gel chromatography (50% EtOAc/CH2Cl2, then 5% MeOH/CH2Cl2). The resulting product was taken up in ether, excess 1N HCl/Ether was added, and the solution was concentrated in vacuo. The titled product, containing tributylphosphine oxide impurity, was used in the next reaction without further purification.

Workup

  1. waitAfter 16 hours
  2. concentrationthe solution was concentrated in vacuo
  3. customThe crude product mixture was purified by silica gel chromatography (50% EtOAc/CH2Cl2
  4. additionexcess 1N HCl/Ether was added
  5. concentrationthe solution was concentrated in vacuo
  6. additionThe titled product, containing tributylphosphine oxide impurity
  7. customwas used in the next reaction without further purification

Sources & evidence

ORD record
ord-02fa8384bf014d41be0ec1c5c65e6d77
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

Loading…